BE-14348 substances, new specific estrogen-receptor binding inhibitors. Production, isolation, structure determination and biological properties.
Streptomyces graminofaciens BA14348, isolated from a soil sample, was found to produce new specific inhibitors of estrogen binding to its receptor. Five related substances, BE-14348A approximately E, were isolated, and their structures were determined by analyses of spectral properties. Of these substances, A was identical with the known flavanone, naringenin. On the other hand, B, C, D and E were all new compounds; the structure of B was determined to be 2(S): 3(S)-3-methyl-4',5,7-trihydroxyflavanone, C was a racemic mixture of 2(S): 3 (R) and 2(R): 3(S)-3-methyl-4',5,7-trihydroxyflavanone; D and E were 8-chloro derivatives of B and C, respectively.
Kondo
H
H
Exploratory Research Laboratories, Banyu Pharmaceutical Co., Ltd., Tokyo, Japan.
Nakajima
S
S
Yamamoto
N
N
Okura
A
A
Satoh
F
F
Suda
H
H
Okanishi
M
M
Tanaka
N
N
D000818:Animals; D001943:Breast Neoplasms; D002845:Chromatography; D004965:Estrogen Antagonists / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005260:Female; D005285:Fermentation; D044950:Flavanones; D005419:Flavonoids / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006367:HeLa Cells; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008855:Microscopy, Electron, Scanning; D008968:Molecular Conformation; D015394:Molecular Structure; D011960:Receptors, Estrogen / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012988:Soil Microbiology; D012995:Solubility; D013237:Stereoisomerism; D013302:Streptomyces / Q000145:classification / Q000378:metabolism / Q000648:ultrastructure; D013552:Swine; D014407:Tumor Cells, Cultured; D014599:Uterus / Q000378:metabolism
D004965:Estrogen Antagonists; D044950:Flavanones; D005419:Flavonoids; D011960:Receptors, Estrogen; C066794:WS 7528; C067073:BE 14348D; C005273:naringenin